ES2709298A1 - Procedimiento para preparar metil ester de acido 3-[(4s)-8-bromo-1-metil-6-(piridin-2-il)-4h-imidazo[1,2-a][1,4]benzodiazepin-4-il]-propionico, y compuestos utiles en ese procedimiento - Google Patents

Procedimiento para preparar metil ester de acido 3-[(4s)-8-bromo-1-metil-6-(piridin-2-il)-4h-imidazo[1,2-a][1,4]benzodiazepin-4-il]-propionico, y compuestos utiles en ese procedimiento

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Publication number
ES2709298A1
ES2709298A1 ES201731210A ES201731210A ES2709298A1 ES 2709298 A1 ES2709298 A1 ES 2709298A1 ES 201731210 A ES201731210 A ES 201731210A ES 201731210 A ES201731210 A ES 201731210A ES 2709298 A1 ES2709298 A1 ES 2709298A1
Authority
ES
Spain
Prior art keywords
procedure
methyl
pyridin
bromo
benzodiazepin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
ES201731210A
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English (en)
Other versions
ES2709298B2 (es
Inventor
Casals Carles Sanchez
Rodriguez Alicia Dobarro
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Moehs Iberica SL
Original Assignee
Moehs Iberica SL
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Moehs Iberica SL filed Critical Moehs Iberica SL
Priority to ES201731210A priority Critical patent/ES2709298B2/es
Priority to EP18788710.4A priority patent/EP3694859A1/en
Priority to PCT/EP2018/077669 priority patent/WO2019072944A1/en
Priority to US16/754,821 priority patent/US11325911B2/en
Publication of ES2709298A1 publication Critical patent/ES2709298A1/es
Application granted granted Critical
Publication of ES2709298B2 publication Critical patent/ES2709298B2/es
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
    • C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
    • C07D243/20—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
    • C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
    • C07D243/24—Oxygen atoms
    • C07D243/26—Preparation from compounds already containing the benzodiazepine skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Procedimiento para preparar metil éster de ácido 3-[(4S)-8-bromo-1-metil-6-(piridin-2-il)-4H-imidazo[1,2-a][1,4]benzodiazepin-4-il]-propiónico, y compuestos útiles en ese procedimiento. La presente invención se relaciona con un procedimiento para preparar metil éster del ácido 3-[(4S)-8-bromo-1-metil-6-(piridin-2-il)-4H-imidazo[1,2-a][1,4]benzodiazepin-4-il]-propiónico, partiendo del éster metílico del ácido 3-[(3S)-7-bromo-2-oxo-5-(piridin-2-il)-2,3-dihidro-1H-[1,4]-benzodiazepin-3-il] propiónico, y nuevos compuestos útiles como intermedios en ese procedimiento, el metil éster de ácido (3S)-3-[7-bromo-2-(2,2-dimetoxipropilamino)-5-piridin-2-il-3H-benzo[e][1,4]diazepin-3-il]propiónico.
ES201731210A 2017-10-13 2017-10-13 Procedimiento para preparar metil ester de acido 3-[(4s)-8-bromo-1-metil-6-(piridin-2-il)-4h-imidazo[1,2-a][1,4]benzodiazepin-4-il]-propionico, y compuestos utiles en ese procedimiento Active ES2709298B2 (es)

Priority Applications (4)

Application Number Priority Date Filing Date Title
ES201731210A ES2709298B2 (es) 2017-10-13 2017-10-13 Procedimiento para preparar metil ester de acido 3-[(4s)-8-bromo-1-metil-6-(piridin-2-il)-4h-imidazo[1,2-a][1,4]benzodiazepin-4-il]-propionico, y compuestos utiles en ese procedimiento
EP18788710.4A EP3694859A1 (en) 2017-10-13 2018-10-11 Method for preparing 3-[(4s)-8-bromo-1-methyl-6-(pyridin-2-yl)-4h-imidazo[1,2-a][1,4]benzodiazepin-4-yl]-propionic acid methyl ester, and compounds useful in said method
PCT/EP2018/077669 WO2019072944A1 (en) 2017-10-13 2018-10-11 PROCESS FOR THE PREPARATION OF 3 - [(4S) -8-BROMO-1-METHYL-6- (PYRIDIN-2-YL) -4H-IMIDAZO [1,2-A] [1,4] METHYL ESTER METHYL ESTER BENZODIAZEPIN-4-YL] -PROPIONIC AND COMPOUNDS USEFUL IN SAID PROCESS
US16/754,821 US11325911B2 (en) 2017-10-13 2018-10-11 Method for preparing 3-[(4S)-8-bromo-1-methyl-6-(pyridin-2-yl)-4H-imidazo[ 1,2-a][1,4]benzodiazepin-4-yl]-propionic acid methyl ester, and compounds useful in said method

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES201731210A ES2709298B2 (es) 2017-10-13 2017-10-13 Procedimiento para preparar metil ester de acido 3-[(4s)-8-bromo-1-metil-6-(piridin-2-il)-4h-imidazo[1,2-a][1,4]benzodiazepin-4-il]-propionico, y compuestos utiles en ese procedimiento

Publications (2)

Publication Number Publication Date
ES2709298A1 true ES2709298A1 (es) 2019-04-15
ES2709298B2 ES2709298B2 (es) 2019-08-21

Family

ID=63878652

Family Applications (1)

Application Number Title Priority Date Filing Date
ES201731210A Active ES2709298B2 (es) 2017-10-13 2017-10-13 Procedimiento para preparar metil ester de acido 3-[(4s)-8-bromo-1-metil-6-(piridin-2-il)-4h-imidazo[1,2-a][1,4]benzodiazepin-4-il]-propionico, y compuestos utiles en ese procedimiento

Country Status (4)

Country Link
US (1) US11325911B2 (es)
EP (1) EP3694859A1 (es)
ES (1) ES2709298B2 (es)
WO (1) WO2019072944A1 (es)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2827125A1 (es) * 2019-11-19 2021-05-19 Moehs Iberica Sl Intermedio util en la preparacion de remimazolam, su procedimiento de obtencion, y su uso en la obtencion de remimazolam
CN114644612A (zh) * 2020-12-17 2022-06-21 成都苑东生物制药股份有限公司 一种苯二氮杂类神经抑制剂中间体化合物的制备方法

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2916845T3 (es) * 2017-02-09 2022-07-06 Assia Chem Ind Ltd Proceso para la preparación de remimazolam y formas en estado sólido de sales de remimazolam
ES2697918A1 (es) * 2017-07-28 2019-01-29 Moehs Iberica Sl Procedimiento para preparar ester metilico del acido 3-[(3s)-7-bromo-2-oxo-5-(piridin-2-il)-2,3-dihidro-1h-[1,4]-benzodiazepin-3-il] propionico, y compuestos utiles en ese procedimiento
ES2709298B2 (es) 2017-10-13 2019-08-21 Moehs Iberica Sl Procedimiento para preparar metil ester de acido 3-[(4s)-8-bromo-1-metil-6-(piridin-2-il)-4h-imidazo[1,2-a][1,4]benzodiazepin-4-il]-propionico, y compuestos utiles en ese procedimiento
ES2803099B2 (es) 2019-07-22 2021-11-08 Moehs Iberica Sl Procedimiento de obtención de besilato de remimazolam amorfo
CN114014839A (zh) * 2021-12-16 2022-02-08 上海再启生物技术有限公司 一种制备瑞马唑仑关键中间体的方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011032692A1 (en) * 2009-09-18 2011-03-24 Paion Uk Limited Process for preparing 3-[(4s)-8-bromo-1-methyl-6-(2-pyridinyl)-4h-imidazol[1,2-a][1,4]benzodiazepine-4-yl]propionic acid methyl ester or the benzene sulfonate salt thereof, and compounds useful in that process
US20160009680A1 (en) * 2013-03-04 2016-01-14 Paion Uk Limited Oxidation reaction excellent in conversion rate

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4001261A (en) 1975-10-20 1977-01-04 The Upjohn Company Process for the production of 1-[(dimethylamino)methyl]-6-phenyl-4H-imidazo[1,2-a][1,4]-benzodiazepine
GB9911152D0 (en) 1999-05-14 1999-07-14 Glaxo Group Ltd Short-acting benzodiazepines
ES2916845T3 (es) 2017-02-09 2022-07-06 Assia Chem Ind Ltd Proceso para la preparación de remimazolam y formas en estado sólido de sales de remimazolam
ES2697918A1 (es) * 2017-07-28 2019-01-29 Moehs Iberica Sl Procedimiento para preparar ester metilico del acido 3-[(3s)-7-bromo-2-oxo-5-(piridin-2-il)-2,3-dihidro-1h-[1,4]-benzodiazepin-3-il] propionico, y compuestos utiles en ese procedimiento
ES2709298B2 (es) 2017-10-13 2019-08-21 Moehs Iberica Sl Procedimiento para preparar metil ester de acido 3-[(4s)-8-bromo-1-metil-6-(piridin-2-il)-4h-imidazo[1,2-a][1,4]benzodiazepin-4-il]-propionico, y compuestos utiles en ese procedimiento

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011032692A1 (en) * 2009-09-18 2011-03-24 Paion Uk Limited Process for preparing 3-[(4s)-8-bromo-1-methyl-6-(2-pyridinyl)-4h-imidazol[1,2-a][1,4]benzodiazepine-4-yl]propionic acid methyl ester or the benzene sulfonate salt thereof, and compounds useful in that process
US20160009680A1 (en) * 2013-03-04 2016-01-14 Paion Uk Limited Oxidation reaction excellent in conversion rate

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2827125A1 (es) * 2019-11-19 2021-05-19 Moehs Iberica Sl Intermedio util en la preparacion de remimazolam, su procedimiento de obtencion, y su uso en la obtencion de remimazolam
CN114644612A (zh) * 2020-12-17 2022-06-21 成都苑东生物制药股份有限公司 一种苯二氮杂类神经抑制剂中间体化合物的制备方法
CN114644612B (zh) * 2020-12-17 2023-04-28 成都苑东生物制药股份有限公司 一种苯二氮杂类神经抑制剂中间体化合物的制备方法

Also Published As

Publication number Publication date
EP3694859A1 (en) 2020-08-19
WO2019072944A1 (en) 2019-04-18
US11325911B2 (en) 2022-05-10
US20200239477A1 (en) 2020-07-30
ES2709298B2 (es) 2019-08-21

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